She Hit On Him Once and He Said No For Reasons. Should She Hit On Him Again?

About a two years ago I developed a searing crush on a guy I knew casually. Through complicated circumstances we ended up working together in my small business. (Me as the owner and him as an independent contractor, so neither of us had any sort of authority or professional leverage over the other.) I asked him out and he replied that it would be a bad idea seeing as how we were working together. I took it as the polite brush-off it very likely was, got over the crush eventually and we have both been professional but friendly. I never brought it up again and neither did he. The crush subsided but the lust remained.

I’m moving out of the country soon, the business is closed, and I probably won’t be able to return to the USA. (Thanks, Trump!) I’m usually good at taking no for an answer, but this dude itches me. Because of clitful thinking, I got hung up on the fact that it took him four days to reply to my message asking him out, while the rest of the time he always replies within minutes. I kind of want to ask one more time, since the circumstances have changed so much since then. I’ll be gone forever in about a month so what do I care? But I feel uncomfortable trying to renegotiate a “no thanks.” Is it okay to ask a second time now that the stated reason for him saying no is gone? Or is that pushy and weird? I just want to tell him I’ve still got the hots for him while I have the chance. I feel like I’ll regret not asking, but I don’t know if it’s okay to do it. (For the record, this is not the kind of person who has any problem saying no.)

To Call Or Not To Call?

It’s highly likely he’s not interested—still—and you’re just setting yourself up for a second rejection. But I will allow it: go ahead and hit on him again. Consider my okay a parting gift. (And fuck Trump, the Electoral College, House and Senate Republicans, Fox News, etc.)

But I gotta say… there’s an awful lot more clitful thinking going on here than you seem to realize.

You didn’t know this guy casually. You knew him professionally—at least you did eventually—and you were in a position of authority over him when you asked him out. And while you say this guy doesn’t have a problem saying no, it took him four days to respond to that message. I doubt he needed to spend four days praying on it before he had an answer. He most likely wanted to say no immediately, TCONTC, but hesitated either because you had leverage over him (you could’ve given him a bad performance review or refused to recommend him to future employers) or because he liked you, even if he didn’t want to fuck you, and didn’t want to hurt your feelings. Or maybe it was a combo of the two, e.g. maybe he genuinely liked you and didn’t want to hurt your feelings and worried you might retaliate against him if you were angered by his rejection. Regardless, TCONTC, you see it as a positive sign that a guy who usually responds to a message within minutes and generally doesn’t have a problem saying no took four days to get back to you with a “no.” That’s definitely some clitful thinking.

And you gotta ask yourself—not your clit—what’s likelier: this guy was dying to fuck you and wouldn’t let himself because you were working together he worked for you or he wasn’t attracted to you and reached for the nearest face-saving, ego-sparing white lie/polite brushoff? The latter seems likelier to me, TCONTC, particularly when you consider that he didn’t get in touch with you after you stopped working together he was no longer working for you. Come on, TCONTC: if he really wanted to fuck you but didn’t for his stated reason… wouldn’t you have heard from him already?

Generally speaking, TCONTC, when someone tells you, “No, I can’t date and/or fuck you because I’m too busy with school/too stressed out at work/too recently out of a relationship,” you should take that “no” as their final answer. The person who rejected you because they’re too busy with work or whatever knows you’re interested and if they wanna circle back once circumstances change, they can always do that. But they almost never do because “I’m too busy with school” or “I’m not my over my ex” is invariably the politest and clearest of brushoffs.

Anyway, TCONTC, the time to not ask this guy out was when he was working for you. And while I think it would be fine for you to ask him out now that he isn’t, I’m pretty sure you’re going to get the same answer. But, hey, better to live with rejection than regret. And sorry about our dumb president.